Just as some context, I spent 24-26 working at an elite single manager then 27-28 at an elite trading firm, then 29-31 as a startup founder then VP at a Series A startup.
At 25-26 at the elite single manager, I made $450K all-in which is roughly what I make now at the startup as a VP. My understanding is this is basically 99th percentile in terms of cash comp at startups and it's basically because I got acqui-hired with unique and highly valuable skills.
What kind of sucks is that if I were ever to leave this startup at work elsewhere, I would immediately take a pay cut of roughly ~50% and make roughly what I made almost a decade ago, which is sort of demoralizing. But the plain reality is that senior exec roles, even at elite startups, don't pay nearly as well as fairly junior roles in elite HFs.
Fwiw, I actually do find the work at the startup more interesting than working at a hedge fund, mostly because it's very "real." It's real in the sense that I have PnL responsibility and feel like I have control over the outcome. I feel like I'm solving a very complicated puzzle that mixes, quantitative, qualitative, managerial/interpersonal and operational considerations. I have a very cool role, but to be honest I feel a bit trapped. If I were to leave my role at any point, I would make an amount that would make me feel like a fuck up. But I also have to work an insane amount - honestly more than I did in banking. Because I honestly think I'd take a paycut of 50% if I were to ever get fired or something I work kind of an insane amount.
(Just in my personal journey I've realized I have a lot of serious mental health issues with respect to work and am probably the work equivalent of "orthorexic" and I also have a serious anger management issue. The biggest benefit to having left finance for a while was actually that it gave me an opportunity to express emotions that I had previously suppressed, like anger. I had already treated issues like anxiety/depression when I was younger, but these were not the root of the issue but rather were second-order effects. I was too afraid to ever be assertive when I was younger, to express personal needs or to set boundaries, but I honestly never noticed this when I was younger since I was too afraid to do so. Working at a startup the power dynamic shifted greatly, which allowed me to realize I had these emotional regulation issues for the first time. I totally hate how I feel trapped now, but also I mean I guess I'm also admitting that I am just the type of person that feels very strong emotions like anger quite easily.)
When I look elsewhere it's really unclear where my skillset would be most highly valued. It's really hard to find anything that pays an amount at all similar to what I used to make in finance. I personally think this experience is super valuable and has helped me see the business world in a whole new way and, plus, it's triggered a new chapter in personal growth I otherwise would have never achieved. The transition was completely necessary in my personal journey as a successful person that is admittedly a bit crazy and eccentric. That said, most finance employers don't see this way. When I interview now for finance roles, I get 90% less interest than I did before. I sort of thought that I could easily go back into HFs, but it doesn't look like that tbh. Once I left the golden path, the number of interviews I got to stick around dwindled rapidly to the point where I don't think I could break back in very easily again at all.
So I've tried to figure out what else pays similarly well but it's pretty tough. Unless you're C-level and maybe 10 years older than I am it's really hard to make what a hedge fund analyst (even a junior analyst) makes. But also maybe I just don't know what's out there. Honestly, my only encounters with rich and successful people are in the finance world since I didn't grow up that rich.
Some options I've considered are:
- Late stage kind of complicated fintech startup as a VP-level exec (similar to what I'm doing now, but maybe somewhere later stage that values my finance skillset more)
- PE operating exec
- Crossover fund, but more on the late stage pre-IPO venture side
- Venture studio
- (I think traditional venture is sorta gross so I wouldn't do that)
- Go back to graduate school of some kind
Curious to hear if any thoughts from people on this forum
I remember your story because it was so unique. Previously you said you liked being an analyst more than being an operator. But here you mentioned the operating role was more interesting and "real", albeit a ton of work. But it also sounds like you won't take a 50% pay cut to do another interesting startup role that's less demanding. I'm curious what your hard stops on each of the 3 variables are: interest, wlb, money?
FWIW I've seen a profile almost identical to yours (5+ years public investing, <1 year VP finance at startup) go back to public investing. It's certainly doable but it's not surprising you're not getting anywhere near the level of interest you'd have had coming right out of Citadel/Coatue...
Let me know if you figure it out. I have a shittier version of your background at every step and am trying to figure it out too. At such a senior level it would be eat what you kill no matter which option you pick, so pick the one you think you're best suited to thrive at.
As a general rule I'd posit that someone who did Citadel/Coatue for 4 years has all the skill sets to do VC or some variation thereof at a senior level - with one possible exception, the strength of your network. That seems like a non-negotiable aspect of the game in VC.
Yeah this makes sense. Part of me just naturally dislikes VC people just too much (because they seem a bit fake / talk about things in too vague of terms) but I agree that within finance roles the ones that offer the most flexibility to switch back to startups are VC roles. You're also right that I don't have a strong enough network to be a VC partner or maybe even principal idk. I'm also naturally bad at relationships and being likable so there's that too. That's why part of me thinks maybe a venture studio would work better since then the actual doing part is more emphasized. Or maybe late stage vc makes more sense at that point idk.
I've seen people go back to public markets too, but it's rare. Being the autist that I am, I actually have a spreadsheet where I analyzed a lot of similar cases to see what the distribution of outcomes was by category. At least in the sample I viewed, it is 2x more common to start a crypto fund than to go back into long/short when you're in my position if you'd like to go back into finance. Kind of almost funny that this is true, but also sort of concerns me. Part of me was like "maybe I should start a crypto fund even though I think crypto might be all a scam" then the FTX thing happened and I decided that I would steer clear of committing myself professionally to the industry since idk I hate scammers.
Realistically what I'm going to do is just keeping working where I am now for as long as I can. If the company raises another round and I stay for around 2 years, I suspect that I'll look a lot better on paper and maybe I get more opportunities out of that idk.
In regard to “VC people being fake” - I definitely agree but would suggest looking into names like Madrona (who also have a venture studio) and Altos. No BS - great culture, and very interesting work overall IMO.
how'd the elite trading firm pay less than the HF...
Couldn't generate PNL presumably
It paid roughly the same amount.
At the elite trading firm, I did a weird role where I was a quasi-trader but not really a trader. I basically would tell them sorta when to do certain quant trades on short-term, news-oriented fundamental events.
How do I get your brain
Probably you need to be somewhere on the autism spectrum and/or have ADHD that manifests as kind of extreme hyper-focus on work (which I didn't realize was a coping mechanism for what is in actuality a difficult-to-resolve issue of how my natural attention is directed, so I have always blamed my employers for this when really it is probably a genetic issue) and difficulties with emotional regulation (which I never noticed until I left finance). When I say hyper-focus, I mean I struggle to do anything that isn't work, but this isn't necessarily because I love work. And that is largely because I struggle in general to initiate new types of tasks but don't struggle to continue tasks that I start. So, for example, I will have extreme difficulty remembering to book a doctor's appointment or text back a friend or take old groceries out of the fridge, but I have no trouble staying up until 2am working on a model for work. When I am not hyper-focused, the alternative is often worse - I end up doing nothing at all. After starting a company that I was ultimately acqui-hired out of, I had a period of 4 months in between and this is where I first noticed this. If I wasn't obsessed obsessed with work, it was a niche non-fiction topic that I could read about for 16 hours. I have a really strong interest in rise/fall stories of American business history and went through a period of reading about that for weeks without stopping. Or it was video games. There was a 1 month period, where I finished a new video game every 3-4 days because I could play for 16 hours straight. But when I didn't do this, I would sit in a pit of despair where I struggled to do anything at all. I would go on long walks for 10 hours a day. Kind of importantly, even when I didn't have work in the way, I still didn't do the things I had always put off in my personal relationships for my personal health etc. For the first time I realized it wasn't work that was the issue - it was how my brain naturally is wired with respect to attention.
It's easy for people to bucket you in with certain finance tropes and for me to accept those categorizations. People want to assume my brain works like "omg money - it's never enough" or "woe is me I was abused as a child and have self esteem issues so I throw myself into work." But neither is true. It's that I have to hyperfocus on things naturally and it's just less bad that it is work than other things, so I naturally threw myself into work.
I attribute myself leaving lucrative roles in the past mostly to me not having enough self-understanding to realize how these mental health issues led me to struggle professionally, build up a lot of anger, then eventually engage in self-destructive behavior (like Juuling, drinking, pushing away others in close relationships). To be clear, my work itself was always excellent, but I struggled emotionally because I blamed my lack of balance on my employers when in reality it had nothing to do with this.
If I was to put my attention into toy trains or something fucking weird, I probably could but it would eventually take up everything in my life. But it's almost like something has to monopolize my attention and the least bad place for it to go in a capitalist society is into work. A lot of neurodiverse people commit suicide because life is honestly hard if your interest happens to be weird shit that doesn't pay well. In my case, I'm lucky that I have a tiny bit more control over where my attention goes than a classically autistic person, but I still unfortunately have this issue where my attention is almost always monopolized by just a few things.
It also wasn't a straightforward case of anxiety/depression or poor self-esteem, so I don't think it was properly understood by healthcare professionals for at least a decade (mostly because gifted/successful neuro-diverse people are very rare. having a unique brain isn't correlated with intelligence and the mental health issues that come out of that present differently than a classic case that doesn't come with high intelligence).
Any recommended books?
Found this really interesting and relatable to me. When a new show or season of something I like comes out, or a video game or a current obsession (right now it's chess), I'm all in and obsessed. I could do it endlessly. In banking, I was pretty hyper focused but now on the entrepreneurial start up side for a REPE firm, I lack motivation or focus and sometimes remembering key numbers or details (part of this may be deal info overload).
I also recently confirmed I have OCD which explains part of the obsessive nature and have been working on that and taking Vyvanse for the ADD/ADHD which some days barely helps. I am also terrible at responding to texts and remembering random chores. How did you learn to refocus your attention and motivation / memory?
A lot of this resonated with me. Can I just ask how tf you managed to spend years in a startup building away without hating it? All the herding cats and working to align people and communicate - how did you stand it, not to mention be successful doing it?
I've seen your posts here before and am in a somewhat similar situation. I was trying to return to this space (on the quant side) after working in tech for several years and getting some recruiter interest. However, there is almost no demand for experienced people who are not PMs, in both the hedge funds and prop places. The pay is not an issue and I know they pay fresh graduates much more than what I get. It seems experience is a bigger problem than age, since I know several friends from my academic research circles who are older but have less experience and got hired easily. For better or worse, academic experience doesn't "count" against you the way finance or tech experience does. I did some interviews but got a clear sense they wanted someone more junior who had no prior knowledge of the space.
Actually, even in tech it's hard to find a new role if you have over 10 years of experience but are not in management, which most will never reach. Managers will often refuse to interview you at that point. High level, non-management roles rarely open up and they want very specific experience that you have to match exactly.
Makes sense. A lot of the career challenges that happen mid-career (around the 10 years mark) start to look super different than fresh out of school, but I actually struggle to find good advice. There's not a similar place as WSO for successful professionals at startups that I'm aware of. Except Blind sorta, but that isn't the same. Most of that is shit posting. WSO helped me a lot when I was younger, but I wish there was a version of WSO more where I am now. I am saying this in response to your post because I appreciated your post and wonder how common what you're saying is, but I don't know how to know what the more common / less common stories are.
Any advice to younger professionals who are 24/25 and in strong megafund PE or blue chip hedge fund seats? A lot of people glamorize the startup and tech world and mention they want to move there after PE but it seems like your advice (from a comp perspective) would be to stick it out?
What did you conclude were the best career strategies in your case then?
I never had a real strategy. I took several one-off opportunities that made sense at the time. The pay was only average but I learned a lot and worked with some great people. The same roles would not exist today or would look very different for someone younger. I also passed on some good opportunities that I should have taken in hindsight. I may try starting a company too if I'm unemployable anywhere else, and have several ideas and VC contacts for it, but never thought I had the right personality or work ethic for it.
This is what happens when you are too smart for your own gig. You left a role that pays %book (trickled down) to a role that is not paying %book. You are trained killer who wants %book. So now is the time to demand equity upside or return to the assassins path.
It will be interesting to see what happens to the recent hires 5-10 years from now. Will the firms eventually discard them for the next batch of college grads? The number of college grads in America will drop sharply after 2026, and at some point in the future, they will essentially run out of inexperienced people to hire.
Can you elaborate?
The birth rates in America (and all developed countries) dropped sharply after 2008, so the number of college graduates will fall after 2026-2030. A lot has been written about this. There will be a lot fewer people to hire with relevant degrees/skills but no experience, which is what many companies want. As the American population gets older and also lives and works longer, eventually (almost) everyone will be "too experienced to hire."
My brother in christ - your startup equity should be worth quite a bit no? 450k cash + maybe 2% of the company, valued at 50-100m, with the chance for an outsized return? That's pretty cool
Also - founding a company is the No1 way to generate wealth - and you are about as backable as they get - would you ever consider starting another company?
Yeah I would consider starting a company again. The issue though is I don't like raising money, because I get too in my head. I would want a co-founder that does that for me so I can focus on being a generalist across product/ops/design/marketing.
The other thing is I think having at least one co-founder that's highly technical helps a lot. So, yes, I would do a venture backed company, but I think the team dynamic has to be right. I have no idea who that team would be since I don't know anyone really that meets the profiles that I would need that is actually interested in startups.
Dm'd
What kind of money are you trying to make? Not sure if you mean you feel like you deserve at least $800k/yr or is this some $20mm long term incentive issue?
The issue with the current startup role isn't money. It's that if I was to leave this startup role, any other similar role would pay 1/2 as much. $400K doesn't feel that bad to me tbh, at least not in an operator role where that makes you among the most highly paid people. (In a finance seat it is different, because then you think of how you performed versus others and you wonder if it's really true that others deserve more money than you. I get that this isn't the most healthy way to look at this, but my point is that it's context dependent and what's fair for better or for worse impacts how I perceive the money). I have been used to having a Plan B in my life, but here I don't really know what that is. $200K would make me feel like a fuckup because I made >=$400K when I was basically still a kid. And the guy who joined at the same time as me / sat next to me at the HF 2 years out of school made $1.5M last year, so making $200K just feels like failure to me. I get this is a mental block, but tbh this is how I pretty strongly feel.
See that's the thing. With your experience I wouldn't be surprised if you could join a unicorn as senior manager / director and make $1m per year. With a lot less stress than the HF guy and a path to growth
Yea, that guy could very well make much less than 1.5mm very soon as well or get canned all together. The money will come if you are focused on it and pursuing the right opportunities. With that said, it sounds like you will want to make about a mil a year roughly to avert your feeling. Choose your path accordingly, it will come (and you won’t even care once you get there and making 2.5x). Also, while some of these very strong established tech cos are down 35-45% y/y consider buying nice chunks of stock.
People in corporate who stick around and climb the ladder have far better-earning potential than the vast majority of hedge fund people with far less stress. The majority of HF analysts are flailing around between getting blown out of pod shops and making $500K. Stick around at Mastercard or something for 20 years and you'll be clearing $500-1M all in consistently.
People on this forum vastly over estimate HF earning potential for the bulk of people that enter the industry vs corporate.
What’s a good source to know what execs at publicly traded companies make? I feel like the level of info is super limited so it’s hard to make plans that are concrete. One nice thing about finance is you sorta know how much people make and when. I know product managers at Facebook make a ton but only because i personally know one and also levels.fyi but I lack similar info for leadership at public companies.
you can just look at publicly listed filings i think? Here's Mastercard's top brass
https://www.bamsec.com/filing/114139122000099/1?cik=1141391&hl=208780:2…
$500k pod shop could easily be $0 and blown out + unemployment - this industry is so overhyped
Moving up the ladder at a F500 requires a lot of politics and a certain personality. Also, it is not just sticking around for 20 years for the career trek you mention you would be moving roles every 2-3 years and basically have to align with a future executive and give your soul to follow them, bet on the right horse and you will be the next in line. Bet on the wrong horse and you may be looking for a new role during the next re-org.
Replace "F500" with "single manager" and its the exact same shit. Only likelihood of outright failure in the latter is much higher
Useful thread, thank you for sharing.
Might seem off-topic but you should take a sabbatical and have a life changing experience.
It'll force you to rethink everything you know and how you do things. The next step will just show itself - it's typically what you find yourself most aligned with wrt to cultural values and principles, then the type of work. I think you're strong enough for it - it'll make your weaknesses less weak and your strengths stronger. You'll also find some meaning in things you already know, have done, or are thinking about doing.
----------- Some personal anecdote that's probably helpful.....
I was on the path to become another version of you. But then I experienced something severely traumatic. It really threw me off - hyper-focus became aggression and erratic impulses. Once your biggest asset turns to your biggest liability, you have to RETHINK everything. It sucks.
But I learned how to breakdown this hyper-focus into its mutually exclusive ingredients - energy, desire, and its down-sides like anxiety, anger, and depression. You can actually negative elements that come along with hyper-focus simply don't have to be there. In Plain English, I'm at a point where I'm learning to trigger at will my hyper-focus with minimal down-sides. I just have to make the battery last longer so I can toggle it on-off when I want without having to recharge too often.
It's trauma or significant failure if you're Shit-Out-of-Luck like me. It's finding a woman you love in the most unexpected place or having a child if you're lucky. It's an ayahuasca trip and meeting God(s) if that's what you're into. Important thing is, once you have one of these experiences, put yourself in a place where you try to replicate the same things that made you good or successful - you won't be able to replicate them: So you have to re-learn them and re-wire your brain.
In the process, you'll find meaning. I traveled a lot during this process I became friends with a ton of interesting people and those who made a career helping those visionaries. Some are very accomplished - 1 guy is about a little shy of being a billionaire and couple people who founded fairly large start-ups and then sold to major tech companies. Some are just starting out. But it's like there's this instinctual understanding that all of us are the same kind of people. But we also know that journey is each of our own. I know it sounds spiritual and very emotional but that's where meaning comes from. Once you have meaning, it's easy to know what's next.
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